ITunes keeps overriding and resetting my media folder change.

Hi,

You need to copy the contents of C:\Users\Main\My Music\iTunes into J:\Dad\iTunes then press and hold down shift when launching iTunes to the create/choose library option. Click Choose, then browse to and open J:\Dad\iTunes\iTunes Library.itl. Correct the media folder location if needed, it may have reset to J:\Dad\iTunes\iTunes Media. Close iTunes and rename your media folder from J:\Dad\iTunes\iTunes Music to J:\Dad\iTunes\iTunes Media, then launch iTunes once more. The media folder should have been updated again, but everything in your library should adjust to the change. Check things still play.

Under File > Library > Organize Library... make sure that Rearrange Files is greyed out, if not tick it and click OK. Now under Edit > Preferences > Advanced turn off Keep organized..., click OK, then turn that option back on again. This should move the stray artist folders from iTunes Media down into iTunes Media\Music. Anything left behind will be disconnected from the library and can be added to it by moving into the Automatically Add to iTunes folder, or discarded if no longer wanted.

tt2

There is a bug in iTunes that, at least for some users, seems to stop the media folder preference from being saved properly. See Make a split library portable - Apple Community and put your library in a shape that isn't affected by the issue, and is easier to backup and move around in future.

tt2

As end users we cannot fix bugs in Apple's software. We're limited to working around them.

Where is your active iTunes Library.itl file now?

Where is your media folder?

How large is the media folder?

How much free space is there on the drive?

With the answers I can give you a simple step by step guide for reorganizing your library so that the media folder path stops changing each time you run iTunes.

tt2